Boronic Acid → N-[5-(cis-3,5-Dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-3-fluoro-4-(2-furanyl)benzenesulfonamide

HRID 130473ノート

反応式

HRID 130473 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[C:16]([N:18]3[CH2:23][C@H:22]([CH3:24])[NH:21][C@H:20]([CH3:25])[CH2:19]3)[CH:15]=[CH:14][C:13]=2[O:26][CH3:27])(=[O:10])=[O:9])=[CH:4][C:3]=1[F:28].[O:29]1[CH:33]=[CH:32][CH:31]=[C:30]1B(O)O.CC(C)([O-])C.[K+].B(O)O>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:25][C@H:20]1[NH:21][C@@H:22]([CH3:24])[CH2:23][N:18]([C:16]2[CH:15]=[CH:14][C:13]([O:26][CH3:27])=[C:12]([NH:11][S:8]([C:5]3[CH:6]=[CH:7][C:2]([C:30]4[O:29][CH:33]=[CH:32][CH:31]=4)=[C:3]([F:28])[CH:4]=3)(=[O:10])=[O:9])[CH:17]=2)[CH2:19]1

参加物

8

反応物 4

HCID 61668Boronic AcidHCID 2734357Furan-2-boronic acidHCID 23665647Potassium tert-butoxideHCID 590070604-Bromo-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-3-fluorobenzenesulfonamide

生成物 1

HCID 24803513N-[5-(cis-3,5-Dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-3-fluoro-4-(2-furanyl)benzenesulfonamide

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒2 回HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
100 °C

実験手順

To a mixture of 4-bromo-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-3-fluorobenzenesulfonamide (E105) (150 mg, 0.32 mmol) and 2-furanylboronic acid (71 mg, 0.64 mmol) in DME (3 ml) was added potassium tert-butoxide (320 mg, 2.9 mmol) and tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.017 mmol) in water (1 ml) and the resulting mixture stirred in a microwave (set at high absorbance) at 100° C. for 30 minutes. The reaction was checked by LC-MS and as starting material was still present (20%) more boronic acid (71 mg, 0.64 mmol) and tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.017 mmol) were added. The mixture was stirred in the microwave (set at high absorbance) at 100° C. for another 30 minutes. The resulting mixture was then purified using an SCX cartridge and mass directed autoprep HPLC to afford the title compound (E307). MS (ES+) m/e 460 [M+H]+.

後処理

  1. additionwere added
  2. stirringThe mixture was stirred in the microwave (set at high absorbance) at 100° C. for another 30 minutes
  3. customThe resulting mixture was then purified

出典と根拠

ORDレコード
ord-f58a848010304805bac13bc5141e28fa
出典データセット
uspto-grants-2008_06
特許番号
US07381728B2

反応ノート

読み込み中…